Sunscreen compounds and compositions containing same and methods for use thereof

ABSTRACT

There is provided a photostable and synergistically enhanced topical sunscreen composition that provides increased substantivity, waterproofness, sweat resistance and rub off resistance. There is further provided methods of enhancing the photostability of a sunscreen active in a topical sunscreen composition, synergistically enhancing the UV absorbance of a topical sunscreen composition having a sunscreen active, and enhancing the substantivity, waterproofness, sweat resistance and rub off resistance in a topical sunscreen composition. The preferred compositions and methods have a sunscreen active, a cosmetically acceptable vehicle, and novel 2-substituted-3,3-diaryl-2-propenoic acid derivatives with [A] a C 16  to C 50  straight or branched chain, substituted or un-substituted, conjugated or non-conjugated hydrocarbon, or [B] a siloxane, polysiloxane, organo-modified polysiloxane residue, a group represented by the formula R 10 [Si(R 10 ) 2 ] n — and R 11  which is a silicone residue derived from a silicone represented by the formula R 11 OH having a molecular weight up to about 30,000, wherein each R 10  is independently selected from the group consisting of alkyl, alkoxy, aryl and aryloxy and n is from 1 to about 500.

BACKGROUND OF THE INVENTION

1. Field of the Invention

The present invention relates to a novel ingredient and the use of same.More particularly, it relates to molecules/compounds that are2-substituted-3,3-diphenyl-2-propenoic acids reacted with [A] a C₁₆ toC₅₀ straight or branched chain, substituted or unsubstituted, conjugatedor non-conjugated hydrocarbon, or [B] a siloxane, polysiloxane ororgano-modified polysiloxane residue. When there is a C₁₆ to C₅₀ chainand it is also a substituted hydrocarbon, the substitutions to thehydrocarbon chain can be an amine, an amide, a hydroxyl, an alkoxy, analkyl, a halogen, a nitrogen, a sulfonyl, nitrile, or phenyl. Even moreparticularly, the present invention relates to the use of the newmolecules in sunscreen compositions to provide protection against theharmful effects caused by ultraviolet radiation. The present inventionalso relates to methods for providing ultraviolet radiation protectionwhile also providing increased UV absorbance, photostabilization,substantivity, waterproofing, water resistance, sweat proofing, sweatresistance, and/or rub off resistance in cosmetic and personal carecompositions.

2. Description of the Related Art

Commercial sunscreen compositions commonly employ a sunscreen active,such as a dibenzoylmethane derivative, e.g. butylmethoxydibenzoylmethane(avobenzone). A common problem associated with some sunscreencompositions is a tendency of sunscreen actives, includingdibenzoylmethane and/or derivatives thereof, to photodegrade over timefrom exposure to UV (ultraviolet) light, e.g. lack ofphotostabilization. This results in an alteration of the UV absorbanceof the composition and, thus, a diminution in sunscreen protection forthe user during extended exposure to sunlight.

U.S. Pat. No. 5,952,391 relates to sunscreen compositions havingdibenzoylmethane sunscreen actives. The compositions have flavone orflavanone derivatives to stabilize the dibenzoylmethane actives.

Current esters of 2-cyano-3,3-diphenyl-2-propenonic acid have shortchain alcohols for ease of use. U.S. Pat. No. 6,416,773 modified thecommercially available esters by reacting the acid with a cyclicalcohol. This change has resulted in crystalline solids with poorsolubility that require the addition of solvents that were not preferredfor optimal efficacy, aesthetics, and stability. Consequently, theseesters are not ideally suited for cosmetic formulations.

Besides photostabilization, suncare formulations also strive for water,perspiration and wear resistance. Additionally, a desired property ofsunscreens is protection from both UVB and UVA wavelengths, as well asincreased coverage of the skin.

It is desired to have a sunscreen composition that is photostable andaffords the claimed sunscreen protection for an extended period of time.It is also desired to have a sunscreen composition that provides: water,perspiration and wear resistance; photostabilization of dibenzoylmethaneand its derivatives and other sunscreens; a synergistic increase in UVabsorbance with dibenzoylmethane derivatives; and a cumulative boost ofUV absorbance in the erythemal action spectra of UV light. It is furtherdesired to have such a photostable sunscreen composition that affords anenhanced degree of sunscreen protection from a broad spectrum of bothUVB and UVA wavelengths, and that also offers improved coverage of theskin.

SUMMARY OF THE INVENTION

It is an object of the present invention to provide a molecule/compoundthat imparts water resistance to a personal care composition, preferablya suncare or insect repellent and/or a combination sunscreen/insectrepellent product.

It is another object of the present invention to provide such amolecule/compound that imparts photostability to a sunscreencomposition.

It is still another object of the present invention to provide such amolecule/compound in which dibenzoylmethane derivatives arephotostabilized by the unique molecule.

It is yet another object of the present invention to provide such amolecule/compound that has a synergistic effect with sunscreens toprovide enhanced UV absorbance upon increased exposure to ultravioletlight.

It is a further object of the present invention to provide a method ofincorporating this molecule/compound into a personal care composition,preferably a suncare product or an outdoor protection product.

It is still a further object of the present invention to provide such amethod in which this molecule/compound is incorporated into a suncareproduct that is water resistant or waterproof, sweat resistant orsweatproof, and/or photostable.

These and other objects and advantages of the present invention areachieved by a composition with improved photostability and enhanced SPF.More preferably, the composition also has water resistant properties.The composition may be cream, gel, liquid, lotion, serum, towletteimpregnated with the composition, mousse, patch, sachet, powder, balm,stick or spray form. The compounds of the present invention have thefollowing general formula (I):

wherein X₁, X₂ and X₃ are independently chosen from a group of thefollowing constituents: cyclic and acyclic, saturated and unsaturated,substituted and unsubstituted, alkyl, aryl, amide, amine, hydroxyl,alkoxyl, halogen, hydrogen, carboxyl, nitrile, nitro, sulfonyl, anionicor cationic groups. Preferred substituents include methyl, ethyl,propyl, cyclopropyl, butyl, cyclobutyl, hexyl, cyclohexyl, heptyl,cycloheptyl, octyl, cyclooctyl, chlorine, bromine, sulfate, phosphate,methoxy, ethoxy, propoxy, butoxy, cyano, cyanato, cyanamino groups, withcyano and cyanato being most preferred;

-   -   X₄ is chosen from NH, NR, O and S, with O being most preferred;    -   Y is chosen from NH, NR, O and S, with O being most preferred.        X₄═O and Y═O are most preferred. R is a C₁ to C₃₀ alkyl,        preferably C₁ to C₁₈, substituted or unsubstituted, preferably        linear; and    -   Z may be either [A] a C₁₆ to C₅₀ straight or branched chain,        substituted or unsubstituted, conjugated or non-conjugated        hydrocarbon or [B] a siloxane, polysiloxane or organo-modified        polysiloxane residue. When there is a C₁₆ to C₅₀ chain and it is        also a substituted hydrocarbon, the substitutions to the        hydrocarbon chain can be an amine, an amide, a hydroxyl, an        alkoxy, an alkyl, a halogen, a nitrogen, a sulfonyl, nitrile, or        phenyl. Preferred compounds have esters of        2-cyano-3,3-diphenyl-2-propenoic acid with a C₁₆ to C₅₀ straight        or branched chain, substituted or un-substituted, conjugated or        non-conjugated hydrocarbon. When there is a C₁₆ to C₅₀ chain, it        is preferred that Z be a C₁₆ to C₄₀ alkyl, C₁₇ to C₅₀ alkyl, C₁₇        to C₄₀ alkyl, C₁₈ to C₅₀ alkyl, C₁₈ to C₄₀ alkyl, C₁₈ to C₅₀        alkyl, C₁₉ to C₄₀ alkyl, C₂₀ to C₅₀ alkyl, C₂₀ to C₄₀ alkyl, C₂₁        to C₅₀ alkyl, C₂₁ to C₄₀ alkyl, C₂₂ to C₅₀ alkyl or C₂₂ to C₄₀        alkyl. Also, any combinations of any alkyls within the C₁₆ to        C₅₀ alkyl range are also contemplated by the present invention.        Particularly preferred are C₂₀ to C₄₀ alkyls.

BRIEF DESCRIPTION OF THE DRAWINGS

These and other embodiments of the present invention will be appreciatedby referring to the drawings that include

FIG. 1 is a graph illustrating the UV absorbance of UVINUL N 539 T; and

FIG. 2 is a graph illustrating the UV absorbance of the presentinvention.

DETAILED DESCRIPTION OF THE INVENTION

The present invention provides a unique class of molecules or compoundsthat can be incorporated into a cosmetic or personal care composition orproduct intended for protecting the skin against UV radiation. Thecomposition can be a suncare product and/or an insect repellent product.More preferably, the composition is a sunscreen product.

The compounds of the present invention have the following generalformula (I):

wherein X₁, X₂ and X₃ are independently chosen from a group of thefollowing constituents: cyclic and acyclic, saturated and unsaturated,substituted and unsubstituted, alkyl, aryl, amide, amine, hydroxyl,alkoxyl, halogen, hydrogen, carboxyl, nitrile, nitro, sulfonyl, anionicor cationic groups. Preferred substituents include methyl, ethyl,propyl, cyclopropyl, butyl, cyclobutyl, hexyl, cyclohexyl, heptyl,cycloheptyl, octyl, cyclooctyl, chlorine, bromine, sulfate, phosphate,methoxy, ethoxy, propoxy, butoxy, cyano, cyanato, cyanamino groups, withcyano and cyanato being most preferred;

-   -   X₄ is chosen from NH, NR, O and S, with O being most preferred;    -   Y is chosen from NH, NR, O and S, with O being most preferred.        X₄═O and Y═O are most preferred. R is a C₁ to C₃₀ alkyl,        preferably C₁ to C₁₈, substituted or unsubstituted, preferably        linear; and Z may be either [A] a C₁₆ to C₅₀ straight or        branched chain, substituted or unsubstituted, conjugated or        non-conjugated hydrocarbon or [B] a siloxane, polysiloxane,        organo-modified polysiloxane residue, a group represented by the        formula: R¹⁰[Si(R¹⁰)₂]_(n)— and R¹¹ which is a silicone residue        derived from a silicone represented by the formula R¹¹OH having        a Molecular Weight up to about 30,000, wherein each R¹⁰ is        independently selected from the group consisting of alkyl,        alkoxy, aryl and aryloxy and n is from 1 to about 500. R¹¹OH can        be a substituted or unsubstituted siloxane or a substituted or        unsubstituted organosiloxane.

The preferred compounds of the present invention are2-substituted-3,3-diphenyl-2-propenoic acid derivatives of generalformula (I):

wherein X₁, X₂ and X₃ are independently chosen from a group of thefollowing constituents: cyclic and acyclic, saturated and unsaturated,substituted and unsubstituted, alkyl, aryl, amide, amine, hydroxyl,alkoxyl, halogen, hydrogen, carboxyl, nitrile, nitro, sulfonyl, anionicor cationic groups. Preferred substituents include methyl, ethyl,propyl, cyclopropyl, butyl, cyclobutyl, hexyl, cyclohexyl, heptyl,cycloheptyl, octyl, cyclooctyl, chlorine, bromine, sulfate, phosphate,methoxy, ethoxy, propoxy, butoxy, cyano, cyanato, cyanamino groups, withcyano and cyanato being most preferred;

-   -   X₄ is O;    -   Y is O.

Z may be either [A] a C₁₆ to C₅₀ straight or branched chain, substitutedor unsubstituted, conjugated or non-conjugated hydrocarbon or [B] asiloxane, polysiloxane, organo-modified polysiloxane residue, a grouprepresented by the formula: R¹⁰ [Si(R¹⁰)₂]_(n)— and R¹¹ which is asilicone residue derived from a silicone represented by the formulaR¹¹OH having a Molecular Weight up to about 30,000, wherein each R¹⁰ isindependently selected from the group consisting of alkyl, alkoxy, aryland aryloxy and n is from 1 to about 500. R¹¹OH can be a substituted orunsubstituted siloxane or a substituted or unsubstituted organosiloxane.

For the compounds, as well as the preferred compounds, the siliconeresidues represented by the formula R¹¹ is R¹⁰[Si(R¹⁰)₂]_(n)—, arederived from the corresponding silicone alcohols, i.e., hydroxy groupcontaining silicones, including silicone alcohols, such as, hydroxysubstituted and hydroxy terminated silicones.

Examples of hydroxyl functional silicones include Dimethiconol, which issold under the trade name of Dow Corning 2-9023, Silicone Fluid NM201-50.000, Unisil SF-R, silanol, methylsilanol, other organomodifiedsilanols, such as, Dow Corning 1248 fluid, and a polydimethylsiloxanepolymer having a terminal silanol functionality, such as, for example,2-1273 fluid from Dow Corning.

When there is a C₁₆ to C₅₀ chain and it is also a substitutedhydrocarbon, the substitutions to the hydrocarbon chain can be an amine,an amide, a hydroxyl, an alkoxy, an alkyl, a halogen, a nitrogen, asulfonyl, nitrile, or phenyl. Preferred compounds have esters of2-cyano-3,3-diphenyl-2-propenoic acid with a C₁₆ to C₅₀ straight orbranched chain, substituted or un-substituted, conjugated ornon-conjugated hydrocarbon. When there is a C₁₆ to C₅₀ chain, it ispreferred that Z be a C₁₆ to C₄₀ alkyl, C₁₇ to C₅₀ alkyl, C₁₇ to C₄₀alkyl, C₁₈ to C₅₀ alkyl, C₁₈ to C₄₀ alkyl, C₁₉ to C₅₀ alkyl, C₁₉ to C₄₀alkyl, C₂₀ to C₅₀ alkyl, C₂₀ to C₄₀ alkyl, C₂₁ to C₅₀ alkyl, C₂₁ to C₄₀alkyl, C₂₂ to C₅₀ alkyl or C₂₂ to C₄₀ alkyl. Also, any combinations ofany alkyls within the C₁₆ to C₅₀ alkyl range are also contemplated bythe present invention. Particularly preferred are C₂₀ to C₄₀ alkyls.

The novel molecules or compounds are2-substituted-3,3-diphenyl-2-propenoic acids reacted with [A] a C₁₆ toC₅₀ straight or branched chain, substituted or unsubstituted, conjugatedor non-conjugated hydrocarbon, or [B] a siloxane, polysiloxane ororgano-modified polysiloxane residue. When there is a C₁₆ to C₅₀ chainand it is also a substituted hydrocarbon, the substitutions to thehydrocarbon chain can be an amine, an amide, a hydroxyl, an alkoxy, analkyl, a halogen, a nitrogen, a sulfonyl, nitrile, or phenyl. The esterscan be used in a variety of personal care products.

Previously described short chain or cyclic esters of2-cyano-3,3-diphenyl-2-propenoic acid absorb predominantly in the UVBspectrum, while long chain esters exhibited absorbance in the UVA andUVB regions as well as improved compatibility with standard cosmeticoils.

It has been unexpectedly discovered according to the present inventionthat a composition having 2-substituted-3,3-diphenyl-2-propenoic acidsreacted with [A] a C₁₆ to C₅₀ straight or branched chain, substituted orunsubstituted, conjugated or non-conjugated hydrocarbon, or [B] asiloxane, polysiloxane or organo-modified polysiloxane residue, whichhave a large molecular configuration, provides superior substantivity,waterproofing and wear resistance as compared to short chain or cyclicesters of 2-cyano-3,3-diphenyl-2-propenoic acid that are currently knownin the art. It was surprisingly found that the preferred embodiment hasan ideal UV absorbance for use in personal UV protection products andprovides broad spectrum protection. It was also surprisingly found thatthe present invention provides for a synergistic increase in UVabsorbance upon long term UV exposure when used in combination withdibenzoylmethane derivatives and/or other sunscreen actives.Additionally, superior photostabilization of the dibenzoylmethanederivative was noted. Previously described short chain or cyclic estersof 2-cyano-3,3-diphenyl-2-propenoic acid absorb predominantly in the UVBspectrum. Furthermore, the above described changes to the Z component ofthe molecule provide a functional molecule that is easy to work with incosmetic formulations.

The present compositions having 2-substituted-3,3-diphenyl-2-propenoicacids reacted with [A] a C₁₆ to C₅₀ straight or branched chain,substituted or unsubstituted, conjugated or non-conjugated hydrocarbon,or [B] a siloxane, polysiloxane or organo-modified polysiloxane residue,provide for increased substantivity, water and rub off resistance inpersonal care preparations. The present composition provides for asynergistic increase in UV absorbance upon long term UV exposure whenused in combination with dibenzoylmethane derivatives and/or othersunscreen actives including Mexoryl SX (terephthalylidene dicamphorsunfonic acid and salts thereof), PABA (para aminobenzoic acid) and itsderivatives, cinoxate, dioxybenzone, homosalate, menthylanthranilate,octocrylene, octyl methoxycinnamate, octyl salicylate, oxybenzone,padimate O, phenylbenzimidazole sulfonic acid, sulisobenzone, titaniumdioxide, zinc oxide, trolamine salicylate, and octyl triazone.Additionally, the composition provides for photostabilization of thedibenzoylmethane derivative. The preferred entity C₂₀-C₄₀ cyano diphenylpropionate provides for substantial UV absorbance in the erythemalaction spectrum. In addition, the preferred entity preferably offers abalanced UVA/UVB ratio of about 0.1 to about 0.9, more preferably about0.25 to about 0.75, and most preferably about 0.4 to about 0.6.

The present composition may have one or more additional sunscreenactives. Such other sunscreen actives may be organic or inorganic,and/or water-soluble or oil soluble. Such actives include those with UVAand/or UVB absorbance from 290 to 400 nanometer solar radiation. Suchsunscreen actives include, but are not limited to, one or more of thefollowing: DEA methoxycinnamate, drometrizole trisiloxane, oxybenzone,octyl methoxycinnamate, octyl salicylate, homomenthyl salicylate, octyldimethyl PABA, TEA salicylate, 4-methyl benzilidene camphor,terephthalydiene dicamphor sulfonic acid, ethyl PABA, hydroxymethylphenyl benzotriazole, methylenebis-benzotriazoyltetramethylbutylphenol, bis-ethylhexyloxyphenolmethoxyphenol triazine, zinc oxide, titanium dioxide or any derivatives,or any combinations thereof. Other useful sunscreen actives includethose disclosed in U.S. Pat. Nos. 5,000,937 and 6,440,402, whichsunscreen actives are incorporated herein by reference.

The compounds according to the present invention can be prepared by thereaction of a compound of formula (I), wherein the group —Y—Z togetherrepresents a single halide, such as a chloride, with the hydroxyfunctional hydrocarbon or siloxane compound, in the presence of anaqueous base when X₄ is oxygen, and, when X₄ is NH, NR or S, underanhydrous conditions, that are generally used for such reactions. Thus,Schotten-Bauman reaction conditions can be used when X₄ is O, andmodified Schotten-Bauman reaction conditions can be used when X₄ is NH,NR, or S, provided anhydrous reaction conditions are maintained.

Preferred bases are those that are capable of removing the hydrogenhalide formed during the reaction. Such bases include hindered amines,such as, 2,2,6,6-tetramethylpiperidenes, diazabicyclooctanes, such as,DABCO, diazabicyclononanes, diazabicyclodecanes, trioctylamine,tridecylamine, tridodecylamine, pentamethyl guanidine, lutidine, protonsponges, such as, 1,10-bis(dimethylamino)naphthalene, basic alumina,basic silica gel, and the like. Aqueous alkali can be used for theSchotten-Bauman reaction.

The present invention provides the suncare formulator with amultifunctional molecule or compound for the formulation of all types ofsuncare products. As discussed above, the present composition canprovide water, sweat and wear resistance, photostabilization ofdibenzoylmethane and its derivatives and other sunscreens, a synergisticincrease in UV absorbance to provide an ideal absorbency when used incombination with dibenzoylmethane derivatives. It also provides acumulative boost of UV absorbance in the erythemal action spectra of UVlight. The present composition also provides protection from both UVBand UVA wavelengths. The large size of this molecule can help lead tomore even coverage of the skin and more active chromophore left on thesurface of the skin.

The large molecular configuration of the compound or molecule of thepresent invention provides for superior substantivity, waterproofing,sweatproofing and wear resistance as compared to the aforementionedshort chain or cyclic esters of 2-cyano-3,3-diphenyl-2-propenoic acidwhich are currently known in the art.

A typical sunscreen active known in the art is octocrylene and has thetrade name UVINUL N 539 T. Octocrylene's chemical structure is:

UVINUL N 539 T is an oil-miscible UV-B filter used in suncarepreparations. As it is miscible with many cosmetic oils, it can beeasily incorporated in the oily phase of an emulsion. Because it ishydrophobic and oil-soluble, it is commonly used for water-resistant andwater-repellant formulations. UVINUL N 539 T is commonly combined withother oil-soluble UV filters to obtain high SPF values. FIG. 1 is agraph illustrating the UV absorbance of UVINUL N 539 T, where the y axisis absorbance and the x axis is wavelength in nanometers.

FIG. 2 is a graph illustrating the UV absorbance of the presentinvention. When comparing the UV absorbance of octocrylene in FIG. 1versus the UV absorbance of the present invention in FIG. 2, the shiftin peak absorbance (i.e., the peak shift to the right in the graph)demonstrates that the present invention provides greater UV-A protectionthan octocrylene.

Table 1 shows the effects of UV exposure on compositions of the presentinvention in combination with the dibenzoylmethane derivative,avobenzone. Samples were exposed to UV radiation produced by a 125WXenon Arc Lamp at 75W power. The UV absorbing properties of thecomposition were measured every five (5) minutes for a total exposure ofone (1) hour. TABLE 1 (Scans taken every 300 seconds) Elapsed Δ UVA/ Δ ΔΔ Cummul. Time UVB UVA UVA ΔCrit. Absorb- Scan (sec.) Δ SPF Ratio PF PF-Lamda ance 1 0 47.6 1.12 65.1 56.5 389.2 194 2 300 70.4 1.07 84.4 78.4389.1 208 3 600 74.0 1.05 84.4 80.9 389.1 209 4 900 75.0 1.05 83.8 81.1389.1 209 5 1200 74.8 1.05 83.2 80.5 389.1 209 6 1500 73.9 1.05 82.579.9 389.1 208 7 1800 74.6 1.05 82.4 80.2 389.1 208 8 2100 74.3 1.0582.2 79.9 389.1 208 9 2400 74.0 1.05 82.2 79.7 389.1 208 10 2700 73.61.05 81.5 79.1 389.1 208 11 3000 73.9 1.05 81.4 79.2 389.1 208 12 330073.8 1.04 81.5 79.7 389.1 208

As shown in Table 1, over the course of twelve scans taken at 300 secondintervals, a 55% improvement in overall SPF activity is demonstratedwith the present invention. There is also a 25% improvement in UV-Aactivity, as well as a 41% improvement in erythemal protection. Thechange in critical lambda or critical wavelength is −0.025%. The changein cumulative absorbance is +6.7%.

Table 2 below sets forth test data from the negative control (i.e.,previously modified (cyclic) octocrylene alone). TABLE 2 Photostabilityin Solution Cyclic Modified Parameter Control Octocrylene Change in SPF−80.41% 121.60% Change in −51.64% −34.00% UVA/UVB Change in UVAPF−91.98% 1167.65% Change in −87.86% 242.42% Erythemal UVAPF Change in−1.84% −1.61% Critical Wavelength Change in −80.65% 103.74% Absorbance

The cyclic modified octocrylene is identified in the aforementioned U.S.Pat. No. 6,416,773.

The present invention is also directed to compositions containing thenovel compounds, especially cosmetic and personal care composition, andmost especially sunscreen compositions. The present compositions mayinclude any cosmetic vehicle known in the art. Suitable vehiclesinclude, but are not limited to, surfactant/cleansing systems, oral careproducts, OTC drugs, artificial tanning, beach/suncare, footcare,patches, wipes, aqueous products, anhydrous products, emulsions, sprayproducts, antiperspirant/deodorant (ap/deo) products, fragrancedproducts, analgesics, insect repellents, jelly fish repellents, poisonivy, oak and sumac protectants, cosmetic sticks, hair care products,conditioners, shampoos, hair colors, styling aids, decorative cosmeticsincluding make-ups, nail polish, pressed powders, mascara, eyeliners,tattoos/body art, lipsticks, lip balms, and concentrates thereof.

The composition can be made into any suitable product form. Such productforms include, but are not limited to, an aerosol, balm, cream, gel,lotion, serum, mousse, patch, pomade, pump spray, roll-on, solution,stick or towelette.

Suitable components of the cosmetic composition may include but are notlimited to one or more of the following: vegetable oils; esters such asoctyl palmitate, C12-15 alkyl benzoate, isopropyl myristate andisopropyl palmitate; ethers such as dicapryl ether and dimethylisosorbide; alcohols such as ethanol and isopropanol; fatty alcoholssuch as cetyl alcohol, stearyl alcohol and behenyl alcohol; isoparaffinssuch as isooctane, isododecane and isohexadecane; silicone oils such asdimethicones, cyclic silicones, and polysiloxanes; hydrocarbon oils suchas mineral oil, petrolatum, isoeicosane and polyisobutene; polyols suchas propylene glycol, ethoxydiglycol, glycerin, butylene glycol,pentylene glycol and hexylene glycol; an elastomer, or any combinationsthereof.

The amount of the novel compound of the present invention to be used ina particular formulation depends on the level of dibenzoylmethanederivative to be stabilized. The compounds of the present invention maybe incorporated into a sunscreen composition at a ratio from 0.05:5.0 to5.0:0.05 on a weight to weight basis of sunscreen to novel compound. Amore preferred ratio is from 0.4:4.0 to 4.0:0.4 and most preferred is1:3.0 to 3.0:1.0.

Optionally, the present composition may include one or more of thefollowing ingredients: anesthetics, anti-allergenics, antifungals,antimicrobials, anti-inflammatories, antiseptics, chelating agents,botanical extracts, colorants, depigmenting agents, emollients,exfollients, film formers, fragrances, humectants, insect repellents(especially ethyl butylacetylaminopropionate (IR3535) and1-piperidinecarboxylic acid 2-(2-hydroxyethyl)-1-methylpropylester andits isomers (Bayer Chemical—Bayrepel KBR 3023), jelly fish repellents,poison ivy, oak and sumac protectants, lubricants, moisturizers,pharmaceutical agents, preservatives, skin protectants, skin penetrationenhancers, stabilizers, surfactants, thickeners, viscosity modifiers,vitamins, or any combinations thereof. Film formers are particularlypreferred.

The present compositions may also have one or more insect repellentactives. Such actives include, but are not limited to, N,Ndiethyl-m-toluamide (DEET), ethyl butylacetylaminopropionate (IR3535 byMerck Co.), 1-piperidinecarboxylic acid2-(2-hydroxyethyl)-1-methylpropylester and its isomers (BayerChemical—Bayrepel KBR 3023),1-{3-cyclohexen-1-ylcarbonyl}-2-methylpiperidine and its isomers(racemate AI3-37220), oil of citronella, soy bean oil, lemon grass oil,geranium/geraniol oil, neem oil, nepetalactone and its isomers and othernatural essential oils, p-menthane-3,8-diol, oil of rue (IBI-246 or anymixtures thereof. Other useful actives are disclosed in U.S. Pat. Nos.5,130,136 and 5,698,209, which actives from those patents areincorporated herein by reference. Preferred insect repellent actives areDEET, IR3535, KBR 3023, nepetalactone and oil of citronella.

Suitable additional film formers may include poly(vinylpyrrolidone/1-triacontene) (Tricontanyl PVP), acrylate copolymer,acrylic C₁₂₋₂₂ alkyl methacrylate copolymer, acrylate/octylacrylamidecopolymer, acrylate/VA copolymer, amodimethicone, AMP/acrylatecopolymer, behenyl beeswax, behenyl/isostearyl, beeswax, butylated PVP,butyl ester of PVM/MA copolymer, calcium/sodium PVM/MA copolymer,dimethicone, dimethicone copolyol, dimethicone/mercaptopropyl methiconecopolymer, dimethicone propylethylenediamine behenate, dimethicolnolethylcellulose, ethylene/acrylic acid copolymer, ethylene/MA copolymer,ethylene/VA copolymer, fluoro C₂₋₈ alkyldimethicone, hexanediol beeswax,C₃₀₋₃₈ olefin/isopropyl maleate/MA copolymer, hydrogenatedstyrene/butadiene copolymer, hydroxyethyl ethylcellulose, isobutylene/MAcopolymer, laurylmethicone copolyol, methyl methacrylate crosspolymer,methylacryloyl ethyl betaine/acrylates copolymer, microcrystalline wax,nitrocellulose, octadecene/MA copolymer, octadecene/maleic anhydridecopolymer, octylacrylamide/acrylate/butylaminoethyl methacrylatecopolymer, oxidized polyethylene, perfluoropolymethylisopropyl ether,polyacrylic acid, polyethylene, polymethyl methacrylate, polypropylene,polyquaternium-10, polyquaternium-11, polyquaternium-28,polyquaternium-4, PVM/MA decadiene crosspolymer, PVM/MA copolymer, PVP,PVP/decene copolymer, PVP/eicosene copolymer, PVP/hexadecene copolymer,PVP/MA copolymer, PVP/VA copolymer, silica dimethyl silylate, sodiumacrylate/vinyl alcohol copolymer, stearoxy dimethicone,stearoxytrimethylsilane, stearyl alcohol, stearylvinyl ether/MAcopolymer, styrene/DVB copolymer, styrene/MA copolymer, tetramethyltetraphenyl trisiloxane, tricontanyl trimethyl pentaphenyl trisiloxane,trimethylsiloxysilicate, VA/crotonates copolymer, VA/crotonates/vinylproprionate copolymer, VA/butyl maleate/isobornyl acrylate copolymer,vinyl caprolactam/PVP/dimethylaminoethyl methacrylate copolymer, andvinyldimethicone, or any combinations thereof.

The present compositions may also have one or more suitable additives.Such additives include, but are not limited to, barium sulfate, silica,nylon polymethylmethacrylate, fiber, plastic, polyethylene,polypropylene, PET, PVC, polyester, protein, colorant/pigment includingphoto-chromic and thermo-chromic colorant/pigment, or any combinationsthereof.

The following is an example of a basic composition according to thepresent invention.

EXAMPLE 1

Ingredient About wt % avobenzone 0.25-3% C₂₀-C₄₀ cyano diphenylpropionate  0.5-6% octinoxate  0.5-7.5% octisalate 0.25-5% emulsifier 0.1-7% co-emulsifier  0.1-5% emollient  0.0-10% insect repellent  5-35% waterproofing polymer  0.0-5% preservative QS water QS to 100%

The following is an example of a particular composition according to thepresent invention.

EXAMPLE 2

Ingredient About wt % avobenzone 0.25-3% C₂₀-C₄₀ cyano diphenylpropionate  0.5-6% oxybenzone  0.5-6% homosalate 0.25-5% emollient 0.0-10% ethanol QS to 100% waterproofing polymer  0.0-5%

The present invention having been described with particular reference tothe preferred forms thereof, it will be obvious that various changes andmodifications may be made herein without departing from the spirit andscope of the present invention as defined in the appended claims.

1. A topical sunscreen composition comprising: at least one sunscreenactive; a cosmetically acceptable vehicle; and a compound of thefollowing general formula (I):

wherein each X₁, X₂ and X₃ are independently selected from the groupconsisting of cyclic and acyclic, saturated and unsaturated, substitutedand unsubstituted, alkyls, aryls, amides, amines, hydroxyls, alkoxyls,halogens, hydrogens, carboxyls, nitrites, nitros, sulfonyls, anionic andcationic groups, X₄ is selected from the group consisting of NH, NR, Oand S, Y is selected from the group consisting of NH, NR, O and S, R isa C₁ to C₃₀ alkyl, substituted or unsubstituted, and Z is selected fromthe group consisting of [A] a C₁₆ to C₅₀ straight or branched chain,substituted or unsubstituted, conjugated or non-conjugated hydrocarbonand [B] a siloxane, polysiloxane, organo-modified polysiloxane residue,a group represented by the formula R¹⁰[Si(R¹⁰)₂]_(n)— and R¹¹ which is asilicone residue derived from a silicone represented by the formulaR¹¹OH having a molecular weight up to about 30,000, wherein each R¹⁰ isindependently selected from the group consisting of alkyl, alkoxy, aryland aryloxy and n is from 1 to about
 500. 2. The composition of claim 1,wherein said X₁, X₂ and X₃ are independently selected from the groupconsisting of methyl, ethyl, propyl, cyclopropyl, butyl, cyclobutyl,hexyl, cyclohexyl, heptyl, cycloheptyl, octyl, cyclooctyl, chlorine,bromine, sulfate, phosphate, methoxy, ethoxy, propoxy, butoxy, cyano,cyanato, and cyanamino groups.
 3. The composition of claim 1, whereinsaid X₄ is O.
 4. The composition of claim 1, wherein said Y is O.
 5. Thecomposition of claim 1, wherein said Z is a C₁₆ to C₅₀ chain.
 6. Atopical sunscreen composition comprising: at least one sunscreen active;a cosmetically acceptable vehicle; and a2-substituted-3,3-diphenyl-2-propenoic acid general formula (I):

wherein each X₁, X₂ and X₃ are independently selected from the groupconsisting of cyclic and acyclic, saturated and unsaturated, substitutedand unsubstituted, alkyls, aryls, amides, amines, hydroxyls, alkoxyls,halogens, hydrogens, carboxyls, nitrites, nitros, sulfonyls, anionic andcationic groups, X₄ is O, Y is O, and Z is selected from the groupconsisting of [A] a C₁₆ to C₅₀ straight or branched chain, substitutedor unsubstituted, conjugated or non-conjugated hydrocarbon and [B] asiloxane, polysiloxane, organo-modified polysiloxane residue, a grouprepresented by the formula R¹⁰[Si(R¹⁰)₂]_(n)— and R¹¹ which is asilicone residue derived from a silicone represented by the formulaR¹¹OH having a molecular weight up to about 30,000, wherein each R¹⁰ isindependently selected from the group consisting of alkyl, alkoxy, aryland aryloxy and n is from 1 to about
 500. 7. The composition of claim 6,wherein the R¹¹OH is selected from the group consisting of a substitutedor unsubstituted siloxane and a substituted or unsubstitutedorganosiloxane.
 8. The composition of claim 6, wherein said X₁, X₂ andX₃ are independently selected from the group consisting of methyl,ethyl, propyl, cyclopropyl, butyl, cyclobutyl, hexyl, cyclohexyl,heptyl, cycloheptyl, octyl, cyclooctyl, chlorine, bromine, sulfate,phosphate, methoxy, ethoxy, propoxy, butoxy, cyano, cyanato, andcyanamino groups.
 9. The composition of claim 6, wherein said Z is a C₁₆to C₅₀ chain.
 10. The composition of claim 9, wherein said C₁₆ to C₅₀chain is a substituted hydrocarbon.
 11. The composition of claim 6,wherein said Z is a C₁₈ to C₅₀ alkyl.
 12. The composition of claim 6,wherein said Z is a C₁₈ to C₄₀ alkyl.
 13. The composition of claim 6,wherein said Z is a C₂₀ to C₅₀ alkyl.
 14. The composition of claim 6,wherein said Z is a C₂₀ to C₄₀ alkyl.
 15. The composition of claim 6,wherein said Z is a C₂₂ to C₅₀ alkyl.
 16. The composition of claim 6,wherein said Z is a C₂₂ to C₄₀ alkyl.
 17. The composition of claim 6,wherein said substituted hydrocarbon has a substitution to thehydrocarbon chain selected from the group consisting of amine, amide,hydroxyl, alkoxy, alkyl, halogen, nitrogen, sulfonyl, nitrile, andphenyl.
 18. The composition of claim 6, wherein said2-substituted-3,3-diphenyl-2-propenoic acid derivative of said generalformula (I) is the ester of 2-cyano-3,3-diphenyl-2-propenoic acid with aC₁₆ to C₅₀ straight or branched chain, substituted or un-substituted,conjugated or non-conjugated hydrocarbon.
 19. The composition of claim18, wherein said ester of 2-cyano-3,3-diphenyl-2-propenoic acid with C₁₆to C₅₋₀ straight or branched chain, substituted or un-substituted,conjugated or non-conjugated hydrocarbon is C₂₀-C₄₀ cyano diphenylpropionate.
 20. The composition of claim 6, wherein the at least onesunscreen active is selected from the group consisting ofdibenzoylmethane, terephthalylidene dicamphor sunfonic acid, PABA,cinoxate, dioxybenzone, homosalate, menthylanthranilate, octocrylene,octyl methoxycinnamate, octyl salicylate, oxybenzone, padimate O,phenylbenzimidazole sulfonic acid, sulisobenzone, titanium dioxide, zincoxide, trolamine salicylate, octyl triazone, DEA methoxycinnamate,drometrizole trisiloxane, oxybenzone, octyl methoxycinnamate, octylsalicylate, homomenthyl salicylate, octyl dimethyl PABA, TEA salicylate,4-methyl benzilidene camphor, ethyl PABA, hydroxy methylphenylbenzotriazole, methylene bis-benzotriazoyltetramethylbutylphenol, zincoxide, titanium dioxide, bis-ethylhexyloxyphenol methoxyphenol triazine,and any derivatives thereof, and any combinations thereof.
 21. Thecomposition of claim 6, wherein the at least one sunscreen active isdibenzoylmethane or a derivative thereof.
 22. The composition of claim21, wherein said 2-substituted-3,3-diphenyl-2-propenoic acid derivativeis present at a ratio from about 0.05:5.0 to about 5.0:0.05 on a weightto weight basis of sunscreen to 2-substituted-3,3-diphenyl-2-propenoicacid derivative.
 23. The composition of claim 6, wherein said vehicle isselected from the group consisting of surfactant/cleansing system, oralcare product, OTC drug, artificial tanning product, beach/suncareproduct, footcare product, patch, wipe, aqueous product, anhydrousproduct, emulsion, spray product, antiperspirant/deodorant product,fragranced product, analgesic, insect repellent, jelly fish repellent,poison ivy, oak and sumac protectant, cosmetic stick, balm, hair careproduct, conditioner, shampoo, hair color, styling aid, decorativecosmetic, make-up, nail polish, pressed powder, mascara, eyeliner,tattoo/body art, lipstick and concentrates thereof, and any combinationsthereof.
 24. The composition of claim 6, further comprising a componentselected from the group consisting of vegetable oil, second ester,ether, alcohol, fatty alcohol, isoparaffin, silicone oil, hydrocarbonoil, polyol, elastomer, water, and any combinations thereof.
 25. Thecomposition of claim 6, wherein said2-substituted-3,3-diphenyl-2-propenoic acid derivative is present in anamount sufficient to synergistically enhance UV absorbance of thecomposition.
 26. The composition of claim 6, wherein said2-substituted-3,3-diphenyl-2-propenoic acid derivative is present in anamount sufficient to enhance the photostability of said at least onesunscreen active.
 27. The composition of claim 6, wherein said2-substituted-3,3-diphenyl-2-propenoic acid derivative is present in anamount sufficient to enhance the water, perspiration and wear resistanceof the composition.
 28. The composition of claim 6, wherein said2-substituted-3,3-diphenyl-2-propenoic acid derivative is present in anamount sufficient to increase UV absorbance in the erythemal actionspectra of UV light of the composition.
 29. The composition of claim 6,wherein said 2-substituted-3,3-diphenyl-2-propenoic acid derivative ispresent in an amount to provide even coverage of skin.
 30. Thecomposition of claim 6, further comprising a film former.
 31. Thecomposition of claim 30, wherein said film former is selected from thegroup consisting of poly(vinyl pyrrolidone/1-triacontene), acrylatecopolymer, acrylic C₁₂₋₂₂ alkyl methacrylate copolymer,acrylate/octylacrylamide copolymer, acrylate/VA copolymer,amodimethicone, AMP/acrylate copolymer, behenyl beeswax,behenyl/isostearyl, beeswax, butylated PVP, butyl ester of PVM/MAcopolymers, calcium/sodium PVM/MA copolymer, dimethicone, dimethiconecopolyol, dimethicone/mercaptopropyl methicone copolymer, dimethiconepropylethylenediamine behenate, dimethicolnol ethylcellulose,ethylene/acrylic acid copolymer, ethylene/MA copolymer, ethylene/VAcopolymer, fluoro C₂₋₈ alkyldimethicone, hexanediol beeswax, C₃₀₋₃₈olefin/isopropyl maleate/MA copolymer, hydrogenated styrene/butadienecopolymer, hydroxyethyl ethylcellulose, isobutylene/MA copolymer,laurylmethicone copolyol, methyl methacrylate crosspolymer,methylacryloyl ethyl betaine/acrylates copolymer, microcrystalline wax,nitrocellulose, octadecene/MA copolymer, octadecene/maleic anhydridecopolymer, octylacrylamide/acrylate/butylaminoethyl methacrylatecopolymer, oxidized polyethylene, perfluoropolymethylisopropyl ether,polyacrylic acid, polyethylene, polymethyl methacrylate, polypropylene,polyquaternium-10, polyquaternium-11, polyquaternium-28,polyquaternium-4, PVM/MA decadiene crosspolymer, PVM/MA copolymer, PVP,PVP/decene copolymer, PVP/eicosene copolymer, PVP/hexadecene copolymer,PVP/MA copolymer, PVP/VA copolymer, silica dimethyl silylate, sodiumacrylate/vinyl alcohol copolymer, stearoxy dimethicone,stearoxytrimethylsilane, stearyl alcohol, stearylvinyl ether/MAcopolymer, styrene/DVB copolymer, styrene/MA copolymer, tetramethyltetraphenyl trisiloxane, tricontanyl trimethyl pentaphenyl trisiloxane,trimethylsiloxysilicate, VA/crotonates copolymer, VA/crotonates/vinylproprionate copolymer, VA/butyl maleate/isobornyl acrylate copolymer,vinyl caprolactam/PVP/dimethylaminoethyl methacrylate copolymer,vinyldimethicone, diethylhexyl sebacate, and any combinations thereof.32. The composition of claim 6, further comprising an insect repellentselected from the group consisting of N,N-diethyl-m-toluamide, ethylbutylacetylaminopropionate, hydroxyethyl 1-piperidinecarboxylic acid2-(2-hydroxyethyl)-1-methylpropylester and its isomers, oil ofcitronella, nepetalactone and its isomers, soy bean oil, lemon grassoil, geranium/geraniol oil, neem oil, p-menthane-3,8-diol, oil of rue,1-{3-cyclohexen-1-ylcarbonyl}-2-methylpiperidine and its isomers, andany combinations thereof.
 33. The composition of claim 6, wherein thecomposition is in the form selected from the group consisting of anaerosol, balm, cream, gel, lotion, serum, mousse, patch, pomade, pumpspray, roll-on, solution, stick, towelette, surfactant/cleansing system,oral care product, OTC drug, artificial tanning product, beach/suncareproduct, footcare product, patch, wipe, aqueous product, anhydrousproduct, emulsion, spray product, antiperspirant/deodorant product,fragranced product, analgesic, insect repellent, jelly fish repellents,poison ivy, oak and sumac protectants, cosmetic stick, balm, hair careproduct, conditioner, shampoo, hair color, styling aid, decorativecosmetic, make-up, nail polish, pressed powder, mascara, eyeliner,tattoo/body art, lipstick and concentrates thereof, and any combinationsthereof.
 34. The composition of claim 6, wherein Z is C₁₆ to C₅₀straight or branched chain, substituted or unsubstituted, conjugated ornon-conjugated hydrocarbon.
 35. A method of enhancing the substantivity,waterproofness, sweat resistance and rub off resistance in a topicalsunscreen composition having a sunscreen active and a cosmeticallyacceptable vehicle, the method comprising introducing into thecomposition an amount of a compound having the following general formula(I):

wherein each X₁, X₂ and X₃ are independently selected from the groupconsisting of cyclic and acyclic, saturated and unsaturated, substitutedand unsubstituted, alkyls, aryls, amides, amines, hydroxyls, alkoxyls,halogens, hydrogens, carboxyls, nitrites, nitros, sulfonyls, anionic andcationic groups, X₄ is selected from the group consisting of NH, NR, Oand S, Y is selected from the group consisting of NH, NR, O and S, and Zis selected from the group consisting of [A] a C₁₆ to C₅₀ straight orbranched chain, substituted or unsubstituted, conjugated ornon-conjugated hydrocarbon and [B] a siloxane, polysiloxane,organo-modified polysiloxane residue, a group represented by the formulaR¹⁰[Si(R¹⁰)₂]_(n)— and R¹¹ which is a silicone residue derived from asilicone represented by the formula R¹¹OH having a molecular weight upto about 30,000, wherein each R¹⁰ is independently selected from thegroup consisting of alkyl, alkoxy, aryl and aryloxy and n is from 1 toabout 500, sufficient to enhance substantivity, waterproofness, and ruboff resistance.
 36. A method of enhancing the substantivity,waterproofness, sweat resistance and rub off resistance in a topicalsunscreen composition having a sunscreen active and a cosmeticallyacceptable vehicle, the method comprising introducing into thecomposition an amount of 2-substituted-3,3-diphenyl-2-propenoic acidderivative having the following general formula (I):

wherein each X₁, X₂ and X₃ are independently selected from the groupconsisting of cyclic and acyclic, saturated and unsaturated, substitutedand unsubstituted, alkyls, aryls, amides, amines, hydroxyls, alkoxyls,halogens, hydrogens, carboxyls, nitrites, nitros, sulfonyls, anionic andcationic groups, X₄ is O, Y is O, and Z is selected from the groupconsisting of [A] a C₁₆ to C₅₀ straight or branched chain, substitutedor unsubstituted, conjugated or non-conjugated hydrocarbon and [B] asiloxane, polysiloxane, organo-modified polysiloxane residue, a grouprepresented by the formula R¹⁰[Si(R¹⁰)₂]_(n)— and R¹¹ which is asilicone residue derived from a silicone represented by the formulaR¹¹OH having a molecular weight up to about 30,000, wherein each R¹⁰ isindependently selected from the group consisting of alkyl, alkoxy, aryland aryloxy and n is from 1 to about 500, sufficient to enhancesubstantivity, waterproofness, and rub off resistance.
 37. The method ofclaim 36, wherein the R¹¹OH is selected from the group consisting of asubstituted or unsubstituted siloxane and a substituted or unsubstitutedorganosiloxane.
 38. The method of claim 36, wherein said2-substituted-3,3-diphenyl-2-propenoic acid derivative of said generalformula (I) is 2-cyano-3,3-diphenyl-2-propenoic acid with C₁₆ to C₅₀straight or branched chain, substituted or un-substituted, conjugated ornon-conjugated hydrocarbon having esters.
 39. The method of claim 38,wherein said 2-cyano-3,3-diphenyl-2-propenoic acid with C₁₆ to C₅₀straight or branched chain, substituted or un-substituted, conjugated ornon-conjugated hydrocarbon is C₂₀-C₄₀ cyano diphenyl propionate.
 40. Themethod of claim 36, wherein the sunscreen active is selected from thegroup consisting of dibenzoylmethane, terephthalylidene dicamphorsunfonic acid, PABA, cinoxate, dioxybenzone, homosalate,menthylanthranilate, octocrylene, octyl methoxycinnamate, octylsalicylate, oxybenzone, padimate O, phenylbenzimidazole sulfonic acid,sulisobenzone, titanium dioxide, zinc oxide, trolamine salicylate, octyltriazone, DEA methoxycinnamate, drometrizole trisiloxane, oxybenzone,octyl methoxycinnamate, octyl salicylate, homomenthyl salicylate, octyldimethyl PABA, TEA salicylate, 4-methyl benzilidene camphor, ethyl PABA,hydroxy methylphenyl benzotriazole, methylenebis-benzotriazoyltetramethylbutylphenol, zinc oxide, titanium oxide,bis-ethylhexyloxyphenol methoxyphenol triazine, and any derivativesthereof, and any combinations thereof.
 41. The method of claim 40,wherein the sunscreen active is dibenzoylmethane or a derivativethereof.
 42. A method of synergistically enhancing the UV absorbance ofa topical sunscreen composition having a sunscreen active and acosmetically acceptable vehicle, the method comprising introducing intothe composition an amount of a compound having the following generalformula (I):

wherein each X₁, X₂ and X₃ are independently selected from the groupconsisting of cyclic and acyclic, saturated and unsaturated, substitutedand unsubstituted, alkyls, aryls, amides, amines, hydroxyls, alkoxyls,halogens, hydrogens, carboxyls, nitrites, nitros, sulfonyls, anionic andcationic groups, X₄ is selected from the group consisting of NH, NR, Oand S, Y is selected from the group consisting of NH, NR, O and S, and Zis selected from the group consisting of [A] a C₁₆ to C₅₀ straight orbranched chain, substituted or unsubstituted, conjugated ornon-conjugated hydrocarbon and [B] a siloxane, polysiloxane,organo-modified polysiloxane residue, a group represented by the formulaR¹⁰[Si(R¹⁰)₂] _(n)— and R¹¹ which is a silicone residue derived from asilicone represented by the formula R¹¹⁰H having a molecular weight upto about 30,000, wherein each R¹⁰ is independently selected from thegroup consisting of alkyl, alkoxy, aryl and aryloxy and n is from 1 toabout 500, sufficient to synergistically enhance UV absorption.
 43. Amethod of synergistically enhancing the UV absorbance of a topicalsunscreen composition having a sunscreen active and a cosmeticallyacceptable vehicle, the method comprising introducing into thecomposition an amount of 2-substituted-3,3-diphenyl-2-propenoic acidderivative having the following general formula (I):

wherein each X₁, X₂ and X₃ are independently selected from the groupconsisting of cyclic and acyclic, saturated and unsaturated, substitutedand unsubstituted, alkyls, aryls, amides, amines, hydroxyls, alkoxyls,halogens, hydrogens, carboxyls, nitrites, nitros, sulfonyls, anionic andcationic groups, X₄ is O, Y is O, and Z is selected from the groupconsisting of [A] a C₁₆ to C₅₀ straight or branched chain, substitutedor unsubstituted, conjugated or non-conjugated hydrocarbon and [B] asiloxane, polysiloxane, organo-modified polysiloxane residue, a grouprepresented by the formula R¹⁰[Si(R¹⁰)₂]_(n)— and R¹¹ which is asilicone residue derived from a silicone represented by the formulaR¹¹OH having a molecular weight up to about 30,000, wherein each R¹⁰ isindependently selected from the group consisting of alkyl, alkoxy, aryland aryloxy and n is from 1 to about 500, sufficient to synergisticallyenhance UV absorption.
 44. The method of claim 43, wherein the R¹¹OH isselected from the group consisting of a substituted or unsubstitutedsiloxane and a substituted or unsubstituted organosiloxane.
 45. Themethod of claim 43, wherein said 2-substituted-3,3-diphenyl-2-propenoicacid derivative of said general formula (I) is2-cyano-3,3-diphenyl-2-propenoic acid with C₁₆ to C₅₀ straight orbranched chain, substituted or un-substituted, conjugated ornon-conjugated hydrocarbon having esters.
 46. The method of claim 45,wherein said 2-cyano-3,3-diphenyl-2-propenoic acid with C₁₆ to C₅₀straight or branched chain, substituted or un-substituted, conjugated ornon-conjugated hydrocarbon is C₂₀-C₄₀ cyano diphenyl propionate.
 47. Themethod of claim 43, wherein the sunscreen active is selected from thegroup consisting of dibenzoylmethane, terephthalylidene dicamphorsunfonic acid, PABA, cinoxate, dioxybenzone, homosalate,menthylanthranilate, octocrylene, octyl methoxycinnamate, octylsalicylate, oxybenzone, padimate O, phenylbenzimidazole sulfonic acid,sulisobenzone, titanium dioxide, zinc oxide, trolamine salicylate, octyltriazone, DEA methoxycinnamate, drometrizole trisiloxane, oxybenzone,octyl methoxycinnamate, octyl salicylate, homomenthyl salicylate, octyldimethyl PABA, TEA salicylate, 4-methyl benzilidene camphor, ethyl PABA,hydroxy methylphenyl benzotriazole, methylenebis-benzotriazoyltetramethylbutylphenol, zinc oxide, titanium dioxide,bis-ethylhexyloxyphenol methoxyphenol triazine, and any derivativesthereof, and any combinations thereof.
 48. The method of claim 47,wherein the sunscreen active is dibenzoylmethane or a derivativethereof.
 49. A method of enhancing the photostability of a sunscreenactive in a topical sunscreen composition comprising introducing intothe composition an amount of a compound having the following generalformula (I):

wherein each X₁, X₂ and X₃ are independently selected from the groupconsisting of cyclic and acyclic, saturated and unsaturated, substitutedand unsubstituted, alkyls, aryls, amides, amines, hydroxyls, alkoxyls,halogens, hydrogens, carboxyls, nitriles, nitros, sulfonyls, anionic andcationic groups, X₄ is selected from the group consisting of NH, NR, Oand S, Y is selected from the group consisting of NH, NR, O and S, and Zis selected from the group consisting of [A] a C₁₆ to C₅₀ straight orbranched chain, substituted or unsubstituted, conjugated ornon-conjugated hydrocarbon and [B] a siloxane, polysiloxane,organo-modified polysiloxane residue, a group represented by the formulaR¹⁰ [Si(R¹⁰)₂]_(n)— and R¹¹ which is a silicone residue derived from asilicone represented by the formula R¹¹OH having a molecular weight upto about 30,000, wherein each R¹⁰ is independently selected from thegroup consisting of alkyl, alkoxy, aryl and aryloxy and n is from 1 toabout 500, sufficient to enhance the photostability of the sunscreenactive.
 50. A method of enhancing the photostability of a sunscreenactive in a topical sunscreen composition comprising introducing intothe composition an amount of 2-substituted-3,3-diphenyl-2-propenoic acidderivative having the following general formula (I):

wherein each X₁, X₂ and X₃ are independently selected from the groupconsisting of cyclic and acyclic, saturated and unsaturated, substitutedand unsubstituted, alkyls, aryls, amides, amines, hydroxyls, alkoxyls,halogens, hydrogens, carboxyls, nitrites, nitros, sulfonyls, anionic andcationic groups, X₄ is O, Y is O, and Z is selected from the groupconsisting of [A] a C₁₆ to C₅₀ straight or branched chain, substitutedor unsubstituted, conjugated or non-conjugated hydrocarbon and [B] asiloxane, polysiloxane, organo-modified polysiloxane residue, a grouprepresented by the formula R¹⁰[Si(R¹⁰)₂]_(n)— and R¹¹ which is asilicone residue derived from a silicone represented by the formulaR¹¹OH having a molecular weight up to about 30,000, wherein each R¹⁰ isindependently selected from the group consisting of alkyl, alkoxy, aryland aryloxy and n is from 1 to about 500, sufficient to enhance thephotostability of the sunscreen active.
 51. The method of claim 50,wherein the R¹¹OH is selected from the group consisting of a substitutedor unsubstituted siloxane and a substituted or unsubstitutedorganosiloxane.
 52. The method of claim 50, wherein said2-substituted-3,3-diphenyl-2-propenoic acid derivative of said generalformula (I) is 2-cyano-3,3-diphenyl-2-propenoic acid with C₁₆ to C₅₀straight or branched chain, substituted or un-substituted, conjugated ornon-conjugated hydrocarbon having esters.
 53. The method of claim 52,wherein said 2-cyano-3,3-diphenyl-2-propenoic acid with C₁₆ to C₅₀straight or branched chain, substituted or un-substituted, conjugated ornon-conjugated hydrocarbon is C₂₀-C₄₀ cyano diphenyl propionate.
 54. Themethod of claim 50, wherein the sunscreen active is selected from thegroup consisting of dibenzoylmethane, terephthalylidene dicamphorsunfonic acid, PABA, cinoxate, dioxybenzone, homosalate,menthylanthranilate, octocrylene, octyl methoxycinnamate, octylsalicylate, oxybenzone, padimate O, phenylbenzimidazole sulfonic acid,sulisobenzone, titanium dioxide, zinc oxide, trolamine salicylate, octyltriazone, DEA methoxycinnamate, drometrizole trisiloxane, oxybenzone,octyl methoxycinnamate, octyl salicylate, homomenthyl salicylate, octyldimethyl PABA, TEA salicylate, 4-methyl benzilidene camphor, ethyl PABA,hydroxy methylphenyl benzotriazole, methylenebis-benzotriazoyltetramethylbutylphenol, zinc oxide, titanium dioxide,bis-ethylhexyloxyphenol methoxyphenol triazine, and any derivativesthereof, and any combinations thereof.
 55. The method of claim 54,wherein the sunscreen active is dibenzoylmethane or a derivativethereof.
 56. A method of enhancing the substantivity, waterproofness,sweat resistance and rub off resistance in a topical sunscreencomposition by applying to the skin of a user a composition of claim 1.57. A method of enhancing the substantivity, waterproofness, sweatresistance and rub off resistance in a topical sunscreen composition byapplying to the skin of a user a composition of claim
 6. 58. A compoundhaving the general formula (I):

wherein each X₁, X₂ and X₃ are independently selected from the groupconsisting of cyclic and acyclic, saturated and unsaturated, substitutedand unsubstituted, alkyls, aryls, amides, amines, hydroxyls, alkoxyls,halogens, hydrogens, carboxyls, nitrites, nitros, sulfonyls, anionic andcationic groups, X₄ is selected from the group consisting of NH, NR, Oand S, Y is selected from the group consisting of NH, NR, O and S, and Zis selected from the group consisting of [A] a C₁₆ to C₅₀ straight orbranched chain, substituted or unsubstituted, conjugated ornon-conjugated hydrocarbon and [B] a siloxane, polysiloxane,organo-modified polysiloxane residue, a group represented by the formulaR¹⁰[Si(R¹⁰)₂]_(n)— and R¹¹ which is a silicone residue derived from asilicone represented by the formula R¹¹OH having a molecular weight upto about 30,000, wherein each R¹⁰ is independently selected from thegroup consisting of alkyl, alkoxy, aryl and aryloxy and n is from 1 toabout
 500. 59. The compound of claim 58, wherein said X₁, X₂ and X₃ areindependently selected from the group consisting of methyl, ethyl,propyl, cyclopropyl, butyl, cyclobutyl, hexyl, cyclohexyl, heptyl,cycloheptyl, octyl, cyclooctyl, chlorine, bromine, sulfate, phosphate,methoxy, ethoxy, propoxy, butoxy, cyano, cyanato, and cyanamino groups.60. The compound of claim 58, wherein said X₄ is O.
 61. The compound ofclaim 58, wherein said Y is O.
 62. The compound of claim 58, whereinsaid Y is NH or NR, wherein R is alkyl.
 63. The compound of claim 58,wherein said Z is a C₁₆ to C₅₀ chain.
 64. The compound of claim 63,wherein said C₁₆ to C₅₀ chain is a substituted hydrocarbon.
 65. Thecompound of claim 58, wherein X₃ is CN, X₄ is O, Y is O and Z is a C₁₆to C₅₀ chain.
 66. The compound of claim 64, wherein said substitutedhydrocarbon has a substitution to the hydrocarbon chain selected fromthe group consisting of amine, amide, hydroxyl, alkoxy, alkyl, halogen,nitrogen, sulfonyl, nitrile, and phenyl.
 67. The compound of claim 58,wherein the compound having general formula (I) is the ester of2-cyano-3,3-diphenyl-2-propenoic acid with C₁₆ to C₅₀ straight orbranched chain, substituted or un-substituted, conjugated ornon-conjugated hydrocarbon.
 68. The compound of claim 67, wherein said2-cyano-3,3-diphenyl-2-propenoic acid with C₁₆ to C₅₀ straight orbranched chain, substituted or un-substituted, conjugated ornon-conjugated hydrocarbon is C₂₀-C₄₀ cyano diphenyl propionate.
 69. Acompound having the general formula (I):

wherein each X₁, X₂ and X₃ are independently selected from the groupconsisting of cyclic and acyclic, saturated and unsaturated, substitutedand unsubstituted, alkyls, aryls, amides, amines, hydroxyls, alkoxyls,halogens, hydrogens, carboxyls, nitrites, nitros, sulfonyls, anionic andcationic groups, X₄ is O, Y is O, and Z is selected from the groupconsisting of [A] a C₁₆ to C₅₀ straight or branched chain, substitutedor unsubstituted, conjugated or non-conjugated hydrocarbon and [B] asiloxane, polysiloxane, organo-modified polysiloxane residue, a grouprepresented by the formula R¹⁰[Si(R¹⁰)₂]_(n)— and R¹¹ which is asilicone residue derived from a silicone represented by the formulaR¹¹OH having a molecular weight up to about 30,000, wherein each R¹⁰ isindependently selected from the group consisting of alkyl, alkoxy, aryland aryloxy and n is from 1 to about
 500. 70. The compound of claim 69,wherein the R¹¹OH is selected from the group consisting of a substitutedor unsubstituted siloxane and a substituted or unsubstitutedorganosiloxane.
 71. The compound of claim 69, wherein said X₁, X₂ and X₃are independently selected from the group consisting of methyl, ethyl,propyl, cyclopropyl, butyl, cyclobutyl, hexyl, cyclohexyl, heptyl,cycloheptyl, octyl, cyclooctyl, chlorine, bromine, sulfate, phosphate,methoxy, ethoxy, propoxy, butoxy, cyano, cyanato, and cyanamino groups.72. The compound of claim 69, wherein said Z is a C₁₆ to C₅₀ chain. 73.The compound of claim 72, wherein said C₁₆ to C₅₀ chain is a substitutedhydrocarbon.
 74. The compound of claim 69, wherein said Z is a C₁₈ toC₅₀ alkyl.
 75. The compound of claim 69, wherein said Z is a C₁₈ to C₄₀alkyl.
 76. The compound of claim 69, wherein said Z is a C₂₀ to C₅₀alkyl.
 77. The compound of claim 69, wherein said Z is a C₂₀ to C₄₀alkyl.
 78. The compound of claim 69, wherein said Z is a C₂₂ to C₅₀alkyl.
 79. The compound of claim 69, wherein said Z is a C₂₂ to C₄₀alkyl.
 80. The compound of claim 69, wherein said substitutedhydrocarbon has a substitution to the hydrocarbon chain selected fromthe group consisting of amine, amide, hydroxyl, alkoxy, alkyl, halogen,nitrogen, sulfonyl, nitrile, and phenyl.
 81. The compound of claim 69,wherein X₃ is CN and Z is a C₁₆ to C₅₀ chain.
 82. The compound of claim69, wherein the compound having general formula (I) is the ester of2-cyano-3,3-diphenyl-2-propenoic acid with C₁₆ to C₅₀ straight orbranched chain, substituted or un-substituted, conjugated ornon-conjugated hydrocarbon.
 83. The compound of claim 82, wherein said2-cyano-3,3-diphenyl-2-propenoic acid with C₁₆ to C₅₀ straight orbranched chain, substituted or un-substituted, conjugated ornon-conjugated hydrocarbon is C₂₀-C₄₀ cyano diphenyl propionate.